Synthesis and anti-inflammatory activity evaluation of some sulfonamide and amidine derivatives of 4-aryl-3-(2 or 4-picolyl)-2-imino-4-thiazolines

Abstract

Condensation of 2- and 4-picolylaminehydrochloride <b style="">2a,b</b> with (un) substituted phenacylthiocyanate <b style="">1a-d</b> gives 4-aryl-3-(2- or 4-picolyl)-2-imino-4-thiazolines <b style="">3a-h</b> in moderate yields. Sulfonamide derivatives <b style="">4a-h</b> have been synthesized by condensation of 4-aryl-3-(2- or 4-picolyl)-2-imino-4-thiazolines <b style="">3a-h</b> with methanesulfonylchloride in good yields. Condensation of 2-cyanopyridine with thiazolines <b style="">3a,</b> <b style="">3e</b> and of 4-cyanopyridine with <b style="">3a</b>, <b style="">c, e</b> and <b style="">h</b> gives amidine derivatives <b style="">5a, b</b> and <b style="">6a-d</b> respectively. Thiazoline derivatives <b style="">3a-h,</b> sulfonamide derivatives <b style="">4a-h</b> and amidine derivatives <b style="">5a, b</b>; <b style="">6a-d</b> are characterized by IR, ¹H NMR, GC-MS spectral data and elemental analysis. Anti-inflammatory activity evaluation of <b style="">3a-h, 4a-d, g-h, 5a</b>,<b style="">b</b> and <b style="">6a-c</b> using carageenan induced paw oedema assay at 50 mg/kg p.o. has been carried out and compound <b style="">6a </b>exhibited anti-inflammatory activity comparable to standard drug ibuprofen.